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La hidroarilación de olefinas catalizada por Rh (I) con perfluoroarenos con déficit de electrones

Zhong-Ming Sun¹, Jing Zhang, Rajith S Manan

¹Department of Chemistry and Molecular Biology, North Dakota State University, Fargo, North Dakota 58102, USA.

Journal of the American Chemical Society

|May 5, 2010

Resumen

Un nuevo sistema de catalizador de rodio promueve adiciones conjugadas directas de perfluoroarenos a las olefinas. Este avance permite una alquilación C-H rara, ofreciendo nuevas vías en la síntesis orgánica.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

La funcionalización directa de los enlaces C-H es un objetivo clave en la química sintética.
La hidroariación de las olefinas con arenas con déficit de electrones sigue siendo un desafío.
Los perfluoroarenos son bloques de construcción importantes, pero a menudo exhiben una baja reactividad.

Objetivo del estudio:

Desarrollar un sistema catalítico eficaz para la adición conjugada directa de perfluoroarenos.
Para explorar una nueva vía de alquilación C-H que involucra arenas con déficit de electrones.
Para investigar las condiciones de reacción para la formación selectiva de productos.

Principales métodos:

Se utilizó un sistema catalizador compuesto por [Rh ((cod)) ((OH)))))) y un ligando de DPPBenzene.
Reacciones realizadas en medios parcialmente acuosos para promover la adición de conjugados.
Condiciones de reacción modificadas para ajustes anidrosos para lograr la olefinación.

Principales resultados:

Promovió con éxito adiciones conjugadas directas de perfluoroarenos a las olefinas.
Demostró un raro ejemplo de hidroarilación de olefinas con arenas con déficit de electrones a través de la activación de C-H.
Se logra la formación selectiva de productos de olefinación en condiciones anidras.

Conclusiones:

El sistema de catalizador de rodio desarrollado es eficaz para las adiciones de conjugado de perfluoroareno.
El estudio presenta una nueva estrategia de alquilación C-H para arenas con déficit de electrones.
Las condiciones de reacción ajustables permiten la síntesis selectiva de productos de adición u olefinación.

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